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Synlett 2018; 29(13): 1711-1716
DOI: 10.1055/s-0037-1610187
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© Georg Thieme Verlag Stuttgart · New York

A Unique Skeletal Rearrangement of a Bicyclo[3.3.1]nonanetrione to a Tetrahydroquinolin-2(1H)-one System

Qi Shen
a   State Key Laboratory of Analytical Chemistry for Life Science, Collaborative Innovation Center of Chemistry for Life Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   Email: wujnju@nju.edu.cn   Email: lijxnju@nju.edu.cn
,
Fang Liu
b   State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   Email: yongliang@nju.edu.cn
,
Yu-Chao Zhang
a   State Key Laboratory of Analytical Chemistry for Life Science, Collaborative Innovation Center of Chemistry for Life Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   Email: wujnju@nju.edu.cn   Email: lijxnju@nju.edu.cn
,
Jie Wang
a   State Key Laboratory of Analytical Chemistry for Life Science, Collaborative Innovation Center of Chemistry for Life Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   Email: wujnju@nju.edu.cn   Email: lijxnju@nju.edu.cn
,
Lei Zhang
a   State Key Laboratory of Analytical Chemistry for Life Science, Collaborative Innovation Center of Chemistry for Life Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   Email: wujnju@nju.edu.cn   Email: lijxnju@nju.edu.cn
,
Yue Wang
a   State Key Laboratory of Analytical Chemistry for Life Science, Collaborative Innovation Center of Chemistry for Life Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   Email: wujnju@nju.edu.cn   Email: lijxnju@nju.edu.cn
,
Hong-Xi Xu
c   School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, P. R. of China
,
Zhuzhou Shao
b   State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   Email: yongliang@nju.edu.cn
,
Yang Cao
d   Institute of New Energy, Shenzhen 518031, P. R. of China
,
Jing Wu*
a   State Key Laboratory of Analytical Chemistry for Life Science, Collaborative Innovation Center of Chemistry for Life Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   Email: wujnju@nju.edu.cn   Email: lijxnju@nju.edu.cn
,
Yong Liang*
b   State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   Email: yongliang@nju.edu.cn
,
Jian-Xin Li*
a   State Key Laboratory of Analytical Chemistry for Life Science, Collaborative Innovation Center of Chemistry for Life Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   Email: wujnju@nju.edu.cn   Email: lijxnju@nju.edu.cn
› Author AffiliationsThis work was supported by National Natural Science Foundation of China (21702101, 21778029, and 21761142001) and the Fundamental Research Funds for the Central Universities in China. Y.L. thanks the ­National Thousand Young Talents Program, Jiangsu Specially­Appointed Professor Plan, and the NSF of Jiangsu Province (BK20170631) in China for financial support. Y.C. acknowledges the support from the Shenzhen Peacock Plan (No.1208040050847074).
Further Information

Publication History

Received: 06 April 2018

Accepted after revision: 27 May 2018

Publication Date:
02 July 2018 (online)

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Abstract

The unexpected formation of a 4-hydroxytetrahydroquinolin-2(1H)-one from a bicyclo[3.3.1]nonanetrione system and an amino alcohol in the presence of TsOH is reported. The mechanism of this transformation was studied by DFT calculations. The reaction provides an entry to the synthesis of highly functionalized 4-hydroxytetrahydroquinolin-2(1H)-ones.

Key words

polyprenylated acylphloroglucinols - skeletal rearrangement - tetrahydroquinolinones - density functional theory - bicyclononanetriones - tetrahydroquinolinones

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610187.
  • Supporting Information
 

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